PINOSTROBIN PRENILATION BY PRENYLBRIMIDE AND NaH

• Main Author: KWARIA (NIM : 20513007), DENNIS
• Format: Theses
• Language: Indonesia
• Subjects: Kimia analitis
• Online Access: https://digilib.itb.ac.id/gdl/view/26491
• Institution: Institut Teknologi Bandung

<p align="justify">Prenyl groups can increase biologic activity of phenolic compounds by increasing its lipophlicity. Increased lipophilicity means higher membrane-compound and protein-compound interactions. Prenylated phenolic compounds are commonly discovered in its prenylated than oxyprenylated form, and limited to few plant family. That means, total synthesis and transformation of existed phenolic compounds will be viable method to acquire prenylated phenolic compound besides isolation. Alkylation on aromatic compounds can be achieved via Friedel-Crafts reaction, Wurtz-Fittig reaction, Mitunobu reaction followed by rearrangement, nucleophilic substitution, and enzymatic reaction using FoPT1 as biocatalyst. Pinostrobin isolated from Temu Kunci (Kaempferia pandurata) were reacted with prenyl bromide using NaH as base, yielding 5 products: 6-prenylpinostrobin; 5-oxyprenyl, 6-prenylpinostrobin; 2’,6’-dioxyprenyl-4’-methoxychalcone; triprenyl cyclohexene chalcone; and 5-oxyprenylpinostrobin It was shown by changing reagents consentration and catalyst equivalence to precursor that 6-prenylpinostrobin and 5-oxyprenylpinostrobin formed simultaneously. In separated reaction, 6-prenylpinostrobin transformed into 5-oxyprenyl,6-prenylpinostrobin, while 5-oxyprenylpinostrobin reacted into 2’,6’-dioxyprenyl-4’-methoxychalcone and triprenyl cyclohexene chalcone. This experiment shows that 6-prenylpinostrobin can be reacted in one reaction step and formed in early hours of reaction. Thus it’s yield can be raised by optimizing early reaction hours. <p align="justify">